Now that he’s at your mercy, don’t let up. He didn’t become a successful executive because he was content to take orders! You can guarantee that he’ll remain a docile, simpering little sissy if you’re not shy about immediately putting him in a chastity belt, giving him massive and regular dosages of feminizing hormones, and begin vibrator-training him.
Tip: Have him move in so that you can more closely administer his transformation from high-powered executive into sexpot little secretary. Keep him securely under wraps until his ‘resignation’ is made public and then prepare him to 'pass' n public.